Hydroxyamine hydrochloride → HCID 178518637, compound

HRID 235307Notes

Reaction equation

HRID 235307 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[NH:8][C:7](=[O:13])[C:6]([NH2:14])=[N:5]2.Cl.N[OH:17]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[NH:8][C:7](=[O:13])[C:6](=[N:14][OH:17])[NH:5]2

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 127731246,7-dichloro-3-aminoquinoxalin-2(1H)-one

Product 1

HCID 178518637HCID 178518637, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

An adaptation of the method of Harsanyi et al., Liebigs Ann. Chem. 190 (1973), was used. A mixture of 6,7-dichloro-3-aminoquinoxalin-2(1H)-one (50 mg, 0.22 mmol) and hydroxylamine hydrochloride (33 mg, 0.47 mmol; Aldrich Co.) in 2 mL of ethanol was heated to reflux. The resulting brown suspension was stirred under reflux for 12 h. The resulting brown suspension was allowed to cool to 25° C. A brown precipitate appeared. The mixture was vacuum filtered and the brown solid was washed with EtOH (5×2 mL) and dried in vacuum at 60° C. overnight to yield 42 mg (79%) of 6,7-dichloro-3-(hydroxyimino)-1,4-dihydroquinoxalin-2-one: mp dec.>270° C. 1H NMR (300 MHz, DMSO-d6) δ 11.306 (br s, 1H, NH), 11.049 (br s, 1H, NH), 10.148 (br s, 1H, NOH), 7.403 (s, 1H, H-5), 7.018 (s, 1H, H-8). Mass: calcd. for C8H5Cl2N3O2 (M+) M/Z 244.9759, found 244.9769.

Workup

  1. temperaturewas heated to reflux
  2. temperatureunder reflux for 12 h
  3. filtrationfiltered
  4. washthe brown solid was washed with EtOH (5×2 mL)
  5. customdried in vacuum at 60° C. overnight

Sources & evidence

ORD record
ord-379bbba0b6a146768d167268bc48a2d0
Source dataset
uspto-grants-1997_01
Patent number
US05597922

Reaction notes

Loading…